South Side Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Browse Select South Side Vacation Homes

Our top choices for South Side vacation homes

Stylish 4BR South Loop Home State 23-202
Fridge, microwave, oven, stovetop

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
The price is CA $171
CA $553 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 4BR South Loop Home State 23-202
Relax & Unwind in This Comfortable 3BR Unit
Interior

Relax & Unwind in This Comfortable 3BR Unit

10.0 out of 10, Exceptional, (4)
"Lakeia was very accommodating throughout our stay."
The price is CA $218
CA $463 total
includes taxes & fees
Sep 9 - Sep 10
Relax & Unwind in This Comfortable 3BR Unit
Studio Apt Comfy & Sunlit
Fridge, microwave, oven, stovetop

Studio Apt Comfy & Sunlit

The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4
Studio Apt Comfy & Sunlit
Hyde Park Haven | 2BR Retreat
Fridge, microwave, oven, stovetop

Hyde Park Haven | 2BR Retreat

8.0 out of 10, Very good, (1)
"Very neat and nicely decorated, only a couple of issues"
The price is CA $190
CA $393 total
includes taxes & fees
Sep 1 - Sep 2
Hyde Park Haven | 2BR Retreat
Contemporary 2BR Apartment in Vibrant Hyde Park
Fridge, microwave, oven, stovetop

Contemporary 2BR Apartment in Vibrant Hyde Park

The price is CA $195
CA $388 total
includes taxes & fees
Sep 16 - Sep 17
Contemporary 2BR Apartment in Vibrant Hyde Park
Furnished 3BR Apt w/ Laundry
3 bedrooms, iron/ironing board, WiFi, bed sheets

Furnished 3BR Apt w/ Laundry

10.0 out of 10, Exceptional, (2)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
The price is CA $162
CA $380 total
includes taxes & fees
Sep 2 - Sep 3
Furnished 3BR Apt w/ Laundry
1BR in Prime Hyde Park Apt
1 bedroom, iron/ironing board, travel crib, WiFi

1BR in Prime Hyde Park Apt

The price is CA $138
CA $291 total
includes taxes & fees
Sep 16 - Sep 17
1BR in Prime Hyde Park Apt
Hyde Park 1BR w/ Charm
1 bedroom, iron/ironing board, travel crib, WiFi

Hyde Park 1BR w/ Charm

The price is CA $127
CA $283 total
includes taxes & fees
Sep 3 - Sep 4
Hyde Park 1BR w/ Charm
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (9)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $197
CA $274 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is CA $244
CA $548 total
includes taxes & fees
Sep 1 - Sep 2
Cozy house in the city
Honeycomb Hideout w/ 2 bedrooms
Fridge, microwave, oven, stovetop

Honeycomb Hideout w/ 2 bedrooms

The price is CA $179
CA $580 total
includes taxes & fees
Sep 1 - Sep 2
Honeycomb Hideout w/ 2 bedrooms
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is CA $312
CA $629 total
includes taxes & fees
Sep 3 - Sep 4
Spacious 3br home near Chicago, fenced yard for pets
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4
TV

Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

10.0 out of 10, Exceptional, (2)
"We liked the location and all of the amenities. "
The price is CA $322
CA $599 total
includes taxes & fees
Sep 8 - Sep 9
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is CA $80
CA $685 total
includes taxes & fees
Sep 23 - Sep 24
4BR Retreat w/ Theater, Game Room & Backyard
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (49)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is CA $209
CA $455 total
includes taxes & fees
Sep 1 - Sep 2
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Travel crib, free WiFi, bed sheets

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is CA $93
CA $519 total
includes taxes & fees
Sep 2 - Sep 3
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is CA $121
CA $293 total
includes taxes & fees
Sep 22 - Sep 23
Great Layout – Spacious 2BR Apt
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is CA $140
CA $412 total
includes taxes & fees
Sep 2 - Sep 3
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is CA $400
CA $908 total
includes taxes & fees
Sep 2 - Sep 3
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Cozy Family Getaway- 4 Blocks From The Beach!
Beach

Cozy Family Getaway- 4 Blocks From The Beach!

The price is CA $151
CA $405 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Family Getaway- 4 Blocks From The Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Find out more about South Side

Find out more about South Side

South Side Vacation Homes information

Number of reviews
9
Accommodation
99 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia